Chatham Rentals
From $699 per night (USD)VRBO
Cozy Chatham home with privacy and nautical decor
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Retreat to the heart of Cape Cod in this restored Cape salt box cottage with 2 bedrooms, offering 1 queen and 2 twins. S ...
From $699 per night (USD)VRBO
From $496 per night (USD)Expedia
Game Room Walk to Nantucket Sound!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16606 - Chatham Charmer: Game Room Walk to Nantucket Sound! The Space: Nestled between Harwich Port and Ch ...
From $496 per night (USD)Expedia
From $689 per night (USD)VRBO
Chatham-Walk to Ridgevale Beach, Winter Rental Option
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
After walking by the beautiful hydrangeas and entering through the front door you will realize this house is much more ...
From $689 per night (USD)VRBO
From $712 per night (USD)Expedia
Stellar Home with Hot Tub & Movie Room!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16614 - Chatham Pearl: Stellar Home with Hot Tub & Movie Room! The Space: Sitting in a quiet neighborhood ...
From $712 per night (USD)Expedia
From $1497 per night (USD)VRBO
Located in a quiet neighborhood, less than a mile from downtown Chatham
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This home is ideal for your family vacation! Located in a quiet neighborhood, it's less than a mile from downtown Chatha ...
From $1497 per night (USD)VRBO
From $307 per night (USD)Expedia
Lovely Home Minutes from Beach in Chatham!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 16605 - Sea Pine Cottage: Lovely Home Minutes from Beach in Chatham! The Space: Tucked into a quiet Chatha ...
From $307 per night (USD)Expedia
From $669 per night (USD)VRBO
Stunning Water Views 2 Decks! By Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16611 - Bucks Creek West: Stunning Water Views 2 Decks! By Beach! The Space: Set at the end of a quiet roa ...
From $669 per night (USD)VRBO
From $452 per night (USD)Expedia
Central AC Close to Beach Dog Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16613 - Maiden Chatham: Central AC Close to Beach Dog Friendly! The Space: Enjoy this beautifully renovate ...
From $452 per night (USD)Expedia
From $480 per night (USD)VRBO
Walk to Ridgevale Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 16612 - Salty Breeze: Walk to Ridgevale Beach! The Space: There is nothing like heading to Cape Cod and en ...
From $480 per night (USD)VRBO
From $536 per night (USD)Expedia
Located on Rail Trail By Beach & Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16617 - Skipping Stone: Located on Rail Trail By Beach & Downtown! The Space: Enjoy the best of Chatham fr ...
From $536 per night (USD)Expedia
From $550 per night (USD)VRBO
4BR+Loft Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town **Video**
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
My family and I live full time in Lexington, MA. We decided to purchase our first vacation home in Chatham, MA in 2008. ...
From $550 per night (USD)VRBO
From $307 per night (USD)Expedia
Old Cape Cod Charm in Chatham MA, 1/4 mile Walking Distance to Hardings Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Quaint 3 bedroom 1 bath cottage, easy 1/4 mile walk to Hardings Beach, one of Chatham's best beaches on Nantucket sound. ...
From $307 per night (USD)Expedia
From $713 per night (USD)VRBO
Cozy Cockle Cove Retreat!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this adorable coastal cottage, perfectly nestled just half a mile from Cockle Cove Beach in Chatham. Offering ...
From $713 per night (USD)VRBO
From $823 per night (USD)Expedia
Beautifully Renovated w/ Access to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Summary: 16626 - Cape Whidah: Beautifully Renovated w/ Access to Beach! The Space: This gorgeous vacation home, loc ...
From $823 per night (USD)Expedia
Click For PricingVRBO
Chatham Luxury! WALK to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Chatham Searenity! BEACH ACCESS! Walk to beautiful beach overlooking monomoy! 2 minutes from Chatham Bars Inn, Chatham l ...
Click For PricingVRBO
From $439 per night (USD)Expedia
Great Location in Chatham Walk to town shop, dine, band concert, cape baseball
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Have a wonderful time on your Cape Cod vacation! Our home includes a new deck for your summer cookouts an outdoor shower ...
From $439 per night (USD)Expedia
From $350 per night (USD)VRBO
Easy Bike Path Access, Dog Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 16649 - Sunny Skies: Easy Bike Path Access, Dog Welcome! The Space: From your doorstep, take a stroll, bik ...
From $350 per night (USD)VRBO
From $604 per night (USD)Expedia
Great Chatham Location w/ Hot Tub, Near Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16650 - The Beach Buoys: Great Chatham Location w/ Hot Tub, Near Beach! The Space: Access to beaches, a qu ...
From $604 per night (USD)Expedia
From $909 per night (USD)VRBO
Home Plate Nestled in Downtown Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Description: *Four bedrooms (plus outbuilding with daybeds sleeping four and heating/cooling…great for teens!) *Beds for ...
From $909 per night (USD)VRBO
From $492 per night (USD)VRBO
Three Bedroom -- Charming, Newly Renovated Cape Cottage - Sandy, Private Ocean Beach Just 500 Ft. Away
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
harming Renovated Cape Cottage with Sandy Private Ocean Beach * * * * See end of this description for informati ...
From $492 per night (USD)VRBO
From $516 per night (USD)VRBO
Great Location Outdoor Space Dog Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16601 - The Salty Seashell: Great Location Outdoor Space Dog Friendly The Space: Set in Chatham, this well ...
From $516 per night (USD)VRBO
From $644 per night (USD)VRBO
Charming Chatham condo-Oyster Pond views, salt-water pool, tennis, water access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy the Chatham breezes off Oyster Pond and take advantage of the best the Cape has to offer whether staying on t ...
From $644 per night (USD)VRBO
From $621 per night (USD)VRBO
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Absolutely beautiful vacation home with upscale furnishings throughout! Giant wraparound porch complete with comfy furni ...
From $621 per night (USD)VRBO
From $711 per night (USD)Expedia
Hot Tub, Fenced Yard & Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16651 - Smooth Sailing: Hot Tub, Fenced Yard & Dog Friendly The Space: Keep it classy this summer and spen ...
From $711 per night (USD)Expedia
From $291 per night (USD)VRBO
Fully Updated Home w/ Great Outdoor Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 16648 - Quail Trail: Fully Updated Home w/ Great Outdoor Space! The Space: This beautifully updated house ...
From $291 per night (USD)VRBO
From $784 per night (USD)VRBO
Walk to the beach! The Salty Breeze sleeps 10; updated house, bikes, beach toys!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Salty Breeze! Come enjoy the perfect vacation spent in Chatham, one of the most desirable summertime dest ...
From $784 per night (USD)VRBO
From $491 per night (USD)VRBO
Spacious w/ Large Outdoor Area Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16637 - The Driftwood: Spacious w/ Large Outdoor Area Fire Pit! The Space: Our beautifully decorated, spac ...
From $491 per night (USD)VRBO
From $267 per night (USD)VRBO
Hidden Gem - Captain's Haven
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest loc ...
From $267 per night (USD)VRBO
From $476 per night (USD)VRBO
Chatham Village - Center - Main Street Center Area
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This is a fantastic - location right off main street in Chatham downtown area - 5 minute walk to Oyster Pond Ocean Inlet ...
From $476 per night (USD)VRBO
From $517 per night (USD)VRBO
Charming/Great Location/Walk to town/baseball field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect location. Minute walk to town, baseball field, fish pier and beach. Bike path is right down the street. This ...
From $517 per night (USD)VRBO
From $1116 per night (USD)VRBO
Enjoy your own private pool in Chatham! (2252)
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Experience the ultimate in coastal luxury at this uniquely designed property in historic South Chatham. Perfect for larg ...
From $1116 per night (USD)VRBO
Click For PricingExpedia
South Chatham cottage walk to beaches, dining, tennis, shops, bike path.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cottage is an affordable Chatham getaway destination for a couple or small family who want to experience Cape Cod. ...
Click For PricingExpedia
From $811 per night (USD)VRBO
Perfectly Content: Walk to Schoolhouse Pond
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
5 Bedroom- 3 Bathroom- Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $811 per night (USD)VRBO
From $654 per night (USD)Expedia
Charming Walk to Beach Chatham-Bayview Cottage 3 BR--Central A/C; Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Every room in this year-round home has been totally renovated and redesigned just a few years ago. The Living Room ha ...
From $654 per night (USD)Expedia
From $665 per night (USD)VRBO
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
STEPS FROM OYSTER POND, SHORT WALK TO TOWN AND CAPE LEAGUE BASEBALL GAMES! This truly is a unique beach house in an excl ...
From $665 per night (USD)VRBO
From $581 per night (USD)Expedia
Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on ...
From $581 per night (USD)Expedia
From $588 per night (USD)VRBO
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy and quiet 3 bedroom, 2 bath Cape style home with an expansive, beautifully landscaped yard…the largest in the area. ...
From $588 per night (USD)VRBO
From $427 per night (USD)VRBO
Beautiful Retreat / Hot tub/ Walk to Ridgevale Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Lovely, sun-filled, completely renovated, 4 bedroom 2 full bath house located within walking distance to beautiful, kid- ...
From $427 per night (USD)VRBO
From $616 per night (USD)VRBO
PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Check in to this beautifully renovated West Chatham ranch, located south of 28 on a quiet cul-de-sac perfect for familie ...
From $616 per night (USD)VRBO
From $759 per night (USD)VRBO
CHATHAM -WALK TO 3 SANDY BEACHES! OPEN Sept 1 -4, Sept 7 there after! RATE DROP!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
CHATHAM - WALK TO 3 BEAUTIFUL SANDY BEACHES ON NANTUCKET SOUND! FREE PARKING AT BOTH FOREST BEACH AND PLEASANT STREET B ...
From $759 per night (USD)VRBO
From $1649 per night (USD)VRBO
Chatham Charm with Pool and Private Beach RPAM006
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Tucked in the private Cannon Hill Neighborhood, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large ...
From $1649 per night (USD)VRBO
From $1175 per night (USD)VRBO
Renovated Chatham Coastal Estate with Water Views and Room for Fourteen
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Fresh 2026 Renovations. Vintage Camp Vibes. Modern Coastal Luxury. Book now to secure your stay at Chatham Waterscape ...
From $1175 per night (USD)VRBO
From $2582 per night (USD)VRBO
Elevate Your Cape Stay: Chatham Luxury with Pool & Beach RPAM026
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Located just .9 miles from the Chatham Bars Inn and 1.3 Miles from Main Street, this 6 bedroom 6 full bath luxury home s ...
From $2582 per night (USD)VRBO
From $1303 per night (USD)Expedia
Private Beach Front Chatham Rental Close To Everything RPAM054
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Nestled in one of the most coveted areas of Cape Cod, 63 Morris Island Road offers everything a discerning tenant could ...
From $1303 per night (USD)Expedia
Click For PricingVRBO
Walk to The Monomoy Wildlife Sanctuary. Great space for relaxing and entertaining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Plan your next vacation by the beach in this charming 3 bedroom, 2 bath home, which comfortably sleeps six with a double ...
Click For PricingVRBO
From $703 per night (USD)VRBO
Visit Cape Cod at a discount after summer! PM us about our 5 star Chatham home!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This completely renovated and newly painted home is located on a private road and just a few minutes walk away from all ...
From $703 per night (USD)VRBO
From $713 per night (USD)VRBO
NEW LISTING Peace and Quiet Pond Front
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Watch the sunset Mill Pond. Surrounded by nature the tranquility is perfection. Just minutes to Chatham Light, Cockle Co ...
From $713 per night (USD)VRBO
From $756 per night (USD)Expedia
Pristine Chatham home walkable to town, CBI, Fish Pier and baseball field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Chatham retreat CLOSE to EVERYTHING, walk to CBI, fish pier, town, baseball field etc. Completely remodeled to perfectio ...
From $756 per night (USD)Expedia
From $2287 per night (USD)VRBO
Hiawatha: 177-CC Gorgeous Chatham Estate with heated pool, walk to Town or Beach
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 15
This home is professionally managed by Pretty Picky Properties Gorgeous Chatham Estate with heated pool, walk to Town o ...
From $2287 per night (USD)VRBO
From $417 per night (USD)Expedia
Close to Bike Path 1 Mile to Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 16673 - Mayflower Retreat: Close to Bike Path 1 Mile to Beaches! The Space: A quick pedal from the Cape Co ...
From $417 per night (USD)Expedia
From $342 per night (USD)VRBO
Updated Beach House Deck Outdoor Shower!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 16670 - A Touch of Blue: Updated Beach House Deck Outdoor Shower! The Space: Nautical colors and floods of ...
From $342 per night (USD)VRBO
From $1064 per night (USD)Expedia
5 Bedroom Chatham Charmer RPAM012
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Located in the highly desirable town of Chatham, this five bedroom, three bath rental home will meet all your vacation n ...
From $1064 per night (USD)Expedia
From $1202 per night (USD)VRBO
Large Chatham Rental w/ 5 Bedrooms w/ 5 Private Bathrooms RPAM007
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This stunning rental home is a vacationer’s dream! Easy and close access to the ponds, bike trails, conservation area a ...
From $1202 per night (USD)VRBO
From $421 per night (USD)Expedia
Large Home w/ Fire Pit and Dogs Welcome!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16674 - Heatherwood Haven: Large Home w/ Fire Pit and Dogs Welcome! The Space: Escape to Chatham, where ba ...
From $421 per night (USD)Expedia
Click For PricingVRBO
Beautiful 3 bedroom Cape with spacious deck and hot tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Lovely modern 3 bedroom home, located on a quiet cul-de-sac is the perfect place for a family vacation. Hop on the bike ...
Click For PricingVRBO
From $2278 per night (USD)Expedia
The Gables: 364-C Chatham Resort Style Estate with Heated Pool, Close to Everything
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 16
This property is professionally managed by Pretty Picky Properties Sleeps 16 Eight Bedrooms, Nine Baths Rents Friday to ...
From $2278 per night (USD)Expedia
From $579 per night (USD)VRBO
Direct Private Beach Access (2290)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the perfect blend of luxury and convenience in this beautiful 2-bedroom, 2-bath waterfront townhouse that offer ...
From $579 per night (USD)VRBO
From $591 per night (USD)Expedia
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Renovated year round 4 bedroom house with bonus office/bunk room with central AC, walking distance to downtown Chatham. ...
From $591 per night (USD)Expedia
From $2426 per night (USD)VRBO
Great Cockle Cove Home!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Family Retreat Destination! Let this 7 bedroom offering 2 queens, 4 twin, 2 full beds and 2 sets of bunk beds, spread o ...
From $2426 per night (USD)VRBO
From $789 per night (USD)VRBO
LOCATION & VIEW - Water Front Home In Chatham Village
- Bedrooms:
- 0
- Bathrooms:
- 3
- Sleeps:
- 6
Fully renovated cottage on little mill pond. Renovation completed may 2016. A 4 minute walk to town of chatham. 3 bedroo ...
From $789 per night (USD)VRBO
From $1211 per night (USD)VRBO
The Barn at Chatham Oaks
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Experience the ultimate getaway at this stunning 7-bedroom retreat, just a mile from Cape Cod’s pristine beaches. Enjoy ...
From $1211 per night (USD)VRBO
From $509 per night (USD)Expedia
Gorgeous Home with Game Room Dog Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16675 - Summer Stunner: Gorgeous Home with Game Room Dog Welcome! The Space: Another Cape Cod vacation mea ...
From $509 per night (USD)Expedia
From $1019 per night (USD)VRBO
Sweeping Water Views, Deeded Beach Access, Pet Friendly and AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Expansive 4 BD / 4 BA Property with AC, and sweeping views of Crows Pond The Space: This home is represent ...
From $1019 per night (USD)VRBO
From $1752 per night (USD)Expedia
Vacation in the heart of Chatham and walk to everything. Oyster Pond Beach is right around the corner!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Experience downtown Chatham! No need to drive when you can walk to everything. This charming rental features a classic f ...
From $1752 per night (USD)Expedia
From $587 per night (USD)VRBO
Marshside Escape: Walk to Cockle Cove
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
3 Bedroom - 3.5 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $587 per night (USD)VRBO
From $387 per night (USD)Expedia
Steps to Private Association Beach. End Unit Condo at Outermost Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Updated Condo at Outermost Harbor. Enjoy amazing views of the famous Chatham sandbars or catch a glimpse of playful seal ...
From $387 per night (USD)Expedia
From $705 per night (USD)VRBO
Location is Everything! Walk to 3 of North Chatham's Most Scenic Salt Water Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Location is everything! Walk to 3 of North Chatham's most scenic salt water beaches and a short trip to Chatham's covete ...
From $705 per night (USD)VRBO
From $2359 per night (USD)Expedia
Sophisticated Chatham Retreat with Private Pool and Spa RPAM093
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your private Chatham retreat, where modern luxury meets classic Cape Cod charm. This stunning four bedroom, f ...
From $2359 per night (USD)Expedia
From $844 per night (USD)VRBO
Waterfront, No Pet Fee, Fenced Yard, Close to Town and Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Soak up the sun while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or ...
From $844 per night (USD)VRBO
From $525 per night (USD)Expedia
0.6 Miles to Beach Great for families!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16677 - Nautical Nest: 0.6 Miles to Beach Great for families! The Space: Seals swim off shore while you so ...
From $525 per night (USD)Expedia
From $598 per night (USD)VRBO
Game Room, Rooftop Deck, Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16678 - Jawsome Getaway: Game Room Rooftop Deck Fire Pit!! The Space: Chatham is the hub of entertainment ...
From $598 per night (USD)VRBO
From $242 per night (USD)Expedia
Charming Chatham Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Prepare to be charmed by this quintessential Cape Cod beach cottage, tucked into a quiet residential neighborhood equidi ...
From $242 per night (USD)Expedia
From $1037 per night (USD)VRBO
Renovated Cape Escape with Forest Beach in your backyard!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Wake up in our renovated home to fresh ocean views. Chatham’s Forest Beach is right in your backyard, where you can spen ...
From $1037 per night (USD)VRBO
From $1165 per night (USD)Expedia
Beautiful and Pristine Rental in South Chatham.. Recently Reduced!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Awesome Three Bedroom Home on a Quiet Cul-de-sac in South Chatham! This beautiful home is perfect for your dream Chat ...
From $1165 per night (USD)Expedia
From $1127 per night (USD)VRBO
Luxurious Home with Pool & Game Room in Cape Cod
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to our newly listed vacation home in Chatham, Cape Cod! This spacious 4-bedroom/4.5-bathroom house is a haven fo ...
From $1127 per night (USD)VRBO
From $1024 per night (USD)Expedia
Stroll Chatham's Historic Downtown / Shops, Dining, Galleries, Etc.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful home located in the heart of Chatham! This lovely home offers all the amenities and decor of a modern house wh ...
From $1024 per night (USD)Expedia
From $755 per night (USD)VRBO
Enjoy Classic Chatham Charm and Easy Stroll to Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Classic Chatham home, recently remodeled, located in the heart of the village and just steps to Mill Pond! It features ...
From $755 per night (USD)VRBO
From $1223 per night (USD)Expedia
Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oh Buoy Oh Buoy A Refined Chatham Retreat Escape to Oh Buoy Oh Buoy, a tastefully renovated Chatham cottage just one m ...
From $1223 per night (USD)Expedia
From $1214 per night (USD)VRBO
Chatham Lovers Lake Waterfront Haven: Private Dock, 4BR/3BA & Lakeside Luxury
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the perfect blend of family adventure and serene “work-from-home” luxury at this stunning 3,154 sq. ft. Lovers ...
From $1214 per night (USD)VRBO
From $1212 per night (USD)Expedia
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Marta (my wife) and I are two Canadians who now call Massachusetts our home. Our lovely place in South Chatham is our ne ...
From $1212 per night (USD)Expedia
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Lovely 3 BR Home in Harbor Coves, North Chatham...Peaceful Setting!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This lovely cape with 3 bedrooms and 2 1/2 baths sits privately on over an acre of land. A classic, antique home filled ...
Click For PricingVRBO
From $648 per night (USD)Expedia
Walk to Beach: Chatham Gem w/ Ocean-View Sunroom!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You’ll be able to hear the crashing waves from every corner of this Chatham, MA, vacation rental. This 3-bedroom, 2-bath ...
From $648 per night (USD)Expedia
From $723 per night (USD)VRBO
Chatham Bliss - Dog Friendly oasis with EV Charging
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our recently updated getaway in charming Chatham, MA! Our pet-friendly retreat is the perfect destination for ...
From $723 per night (USD)VRBO
From $2291 per night (USD)Expedia
Pool and large yard!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
We invite you to spend time with your family and enjoy all that Chatham has to offer at this beautiful North Chatham hom ...
From $2291 per night (USD)Expedia
From $3687 per night (USD)VRBO
Sophisticated Chatham Oasis with Pool & Spa RPAM062
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to 84 Doane Road in Chatham, MA, where opulence meets comfort and convenience. Nestled in a prime location just ...
From $3687 per night (USD)VRBO
From $660 per night (USD)VRBO
Star of the Sea - Newly Renovated Cape House .9Miles from the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Escape to Star of the Sea a charming 2 story Cape house in South Chatham, MA. This delightful newly renovated rental fea ...
From $660 per night (USD)VRBO
From $658 per night (USD)VRBO
Cockle Cottage - Renovated Chatham Cape House .9 Miles from Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Indulge in a memorable stay at Cockle Cottage in Chatham, MA. This inviting rental boasts 2 bedrooms, 1 bathroom and com ...
From $658 per night (USD)VRBO
From $1091 per night (USD)VRBO
Enjoy a relaxing retreat. Easy access: Beaches, Bike Path, & Great restaurants.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This charming, tastefully decorated, and bright home includes a cheerful yellow fully equipped kitchen with a unique isl ...
From $1091 per night (USD)VRBO
From $557 per night (USD)VRBO
Cape Escape - Family-Friendly Chatham Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom- 2 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $557 per night (USD)VRBO
From $647 per night (USD)Expedia
Classic Cape House Walking Distance to the Beach - Many recent upgrades
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Recent upgrades: Complete interior painted (March 2025); Main dining table refinished (April 2025); Downstairs bathroom ...
From $647 per night (USD)Expedia
From $1651 per night (USD)VRBO
Upscale Elegance, Steps from Ridgevale Beach!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your coffee overlooking Ridgevale Beach! Enjoy spectacular and expansive water views in this beautifully appointed ...
From $1651 per night (USD)VRBO
From $1079 per night (USD)VRBO
Beautifully renovated home, outdoor space, pet considered
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Sea~a~Bella - Your perfect Chatham family vacation is here. You will find three beautiful, scenic beaches within walking ...
From $1079 per night (USD)VRBO
From $608 per night (USD)VRBO
Sarah-N-Dipity: Cozy Cottage Near Ridgevale Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedrooms - 1 Bathroom - Sleeps 4 A 3-night midweek stay - Monday to Wednesday - is offered at this home during the pea ...
From $608 per night (USD)VRBO
From $1493 per night (USD)VRBO
Enjoy a Cape Cod beach vacation on the beach in picturesque Chatham.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Have the vacation of your dreams in this oceanfront beach cottage with beautiful water views, located on Morris Island i ...
From $1493 per night (USD)VRBO
From $377 per night (USD)VRBO
1 Mi to Sand! Mid-Cape Chatham w/ Furnished Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to a classic coastal getaway at this charming Chatham vacation rental. Located 1 mile from the shore and steps f ...
From $377 per night (USD)VRBO
From $658 per night (USD)Expedia
Roof Deck, Walk to Forest Beach, Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16679 - Inn Bloom: Roof Deck, Walk to Forest Beach, Fire Pit! The Space: Inn Bloom is perched on a small h ...
From $658 per night (USD)Expedia
From $745 per night (USD)VRBO
Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friend
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16680 - Seaside Sapphire: Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friendly! ...
From $745 per night (USD)VRBO
From $467 per night (USD)Expedia
Quintessential Cape directly on the Cape Cod Rail, Dog Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16682 - Nob Hill: Quintessential Cape directly on the Cape Cod Rail, Dog Friendly! The Space: In this Quin ...
From $467 per night (USD)Expedia
From $373 per night (USD)VRBO
Movie Theater Room, Direct Access to Bike Trail!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: 16681 - Summer On: Movie Theater Room, Direct Access to Bike Trail! The Space: Escape to this charming Cha ...
From $373 per night (USD)VRBO
From $400 per night (USD)VRBO
Let your Chatham traditions begin here!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
From the moment you walk into our charming single floor cottage you are invited to relax and unwind. Whether it is coffe ...
From $400 per night (USD)VRBO